


Ghosts of Girlfriends Past

by 70sBabe



Category: Gilmore Girls
Genre: Canon Divergence, F/M, Jess' POV, Literati, My sweet son, a list (sort of), disregarding AYITL, jess is angsty, justice for jess mariano
Language: English
Status: Completed
Published: 2018-02-16
Updated: 2018-02-16
Packaged: 2019-03-19 14:18:12
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,012
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13706202
Author URL: https://archiveofourown.org/users/70sBabe/pseuds/70sBabe
Summary: you didn't think Rory was the only girl Jess ever dated, did you?





	Ghosts of Girlfriends Past

_i. Becky Anderson_

Jess was six years old and had just learned what a girlfriend was. He strode confidently up to the lunch table Becky Anderson was sitting at. Becky had blonde hair that she always wore in braids and shiny red tennis shoes that Jess liked a lot.

“Wanna be my girlfriend?” he said, staring at her.

“Okay,” she shrugged, turning back to her lunch. “Want one of my apple slices?”

“Yeah, thanks.”

They split up two days later. Jess wasn’t too broken up about it.

 

 

_ii. Lara Crenshaw_

Jess was thirteen years old and head-over-heels in love with Lara Crenshaw. She sat in front of him in Biology and was always tossing her long brown hair around. Jess had to stop himself from reaching out and touching it. Lara was beautiful and smart and she always smiled at Jess when she saw him in the hallways. When you’re thirteen, that’s all you need to fall in love with someone.

Jess spent weeks trying to get his nerve up to ask her out, tossing and turning at night as he pictured all the different and horrible ways in which she could reject him. He fell in love with her in October; he finally asked her out in March.

They were supposed to be working quietly on their lab reports when Jess carefully tossed a folded up piece of paper on Lara’s desk.

 

_do you like me?_

  _YES                    NO_

 

Jess jiggled his leg up and down nervously, already regretting his brief flash of courage. What if she circled no? What was he gonna do then? His thoughts were interrupted by Lara tossing the note back to him.

YES was circled in purple sparkly gel pen. Jess smiled so big it made his face hurt.

They dated from March to June. They went to the movies a lot, never talking much, just sitting nervously together in the dark theater with sweaty palms. She was Jess’ first kiss.

 

 

_iii. Christine Thomas_

Jess was fifteen years old and had one thing on his mind: girls. Jess read a lot of books; he knew the usual spiel about raging hormones and all that. Didn’t mean he could control his thoughts.

Christine Thomas had the biggest boobs in the freshmen class at Stuyvesant High School and purple streaks in her hair. She wore a leather jacket and ripped-up tights and Jess thought she was the coolest chick he’d ever seen.

They started “dating” after a particularly boring detention that they had both been sent to. As they both walked through the main hallway, Jess’ sneakers squeaking on the linoleum, Christine had said casually, “Hey, Mariano, wanna make out in the janitor’s closet?”

He did.

They didn’t really go on dates; more like they would both happen to show up at the same party or concert and then, at the end of the night, they would make out sloppily in some dark corner. They smoked cigarettes in alleyways, snuck beer from their parents’ fridges, and drank it on the roof of her building while they looked at the city lights. She called him Mariano, he called her Chris. She was the first girl Jess ever got to second base with.

One day, she didn’t come to school. Jess found out she ran off to Boston with some guy named Jim who she’d also been hooking up with. He wasn’t mad.

 

  
_iv. Shane Matthews_

Jess was seventeen years old and was pretty sure he was in love, _real_ love, for the first time in his life. Rory Gilmore; big blue eyes, shiny brown hair, and a passion for literature that rivaled his own. Too bad she was dating some Neanderthal and apparently didn’t give a crap about what he felt. She had kissed him at the beginning of the summer, then promptly disappeared to DC. Jess had tried not to get his hopes up, but he couldn’t help himself; he could really _see_ something with this girl, something real. But as the days wore on and her call never came, Jess decided to harden his heart. Rory had made her choice. He had to make one of his own.

He met Shane at a bonfire that Rick Lennox had in his backyard. Jess didn’t even know why he went; it’s not like he was the social butterfly of Stars Hollow High. But he was there, standing silently a few feet away from the fire and nursing a beer, when Shane had walked right up to him.

“You’re Jess, right?”

“In the flesh.”

“I’m Shane.”

“Fascinating.” Jess rolled his eyes. “Did you need something or-?”

Shane cocked her head, eyes narrowed, as if she was sizing him up. Then, before he could tell her to buzz off, Shane had her arms around his neck and was kissing him enthusiastically. Jess’ eyes widened in surprise, but he quickly responded in kind, putting his hands on her hips and tugging her closer.

They spent the rest of the night making out. Not a lot of talking, but Jess was okay with that. He got the feeling Shane was not exactly the most engaging of conversationalists. But she wasn’t Rory and she was a girl who wanted to kiss him and Jess liked that.

They started dating that summer but, just like with Christine, “dating” was a loose term. They would go to the movie theater in Hartford and make out in the last row. They would go to her house, order a pizza, and make out until her mom got home from work. They would go to the apartment and make out on the couch while reruns of _I Love Lucy_ played in the background.

Jess couldn’t have told you what her middle name was. He had no idea what her hobbies were, if she had any. He didn’t know what her favorite subject in school was, or what her dog’s name was, or her favorite movie (Rory’s middle name was Leigh, she liked to read and watch movies with her mom and do school work and that was really about it. She loved English, she had had a fish named Jane Eyre, and she had too many favorite movies to count. Jess hated that he knew all that).

It was a ridiculous farce of a relationship, but Jess felt it was all worth it when he saw the look on Rory’s face once she realized he hadn’t just sat around waiting for her. He took a twisted, vindictive pleasure in seeing the pain that flashed in her eyes every time she saw him and Shane together.

When Dean dumped Rory at that insane 24-hour dance thing, Shane had laughed. Dean had stormed off, Rory had walked out the door with a shell-shocked look on her face, and Jess, who had stood up as soon as Dean had started yelling at Rory (as if he thought he needed to protect her or something. Stupid, right?), was frozen in place. He couldn’t believe it had actually happened. And then Shane had snickered.

“You know, I didn’t really wanna come to this thing, but seeing Mr. and Mrs. Perfect break up live and in color made it all worth it,” Shane leaned back against the bleachers. Jess turned to her, still feeling like he was dreaming.

“Yeah….I gotta….” he trailed off, turning back to the gym doors, half-expecting to see Rory and Dean standing there, doing the whole kiss-and-make-up routine.

“Jess?” Shane’s voice brought him back to reality.

“I gotta go,” Jess said suddenly.

“What? Where?”

“The, uh….the diner. Luke needs me to….work.” Jess winced at how clumsy his words sounded, but Shane just shrugged and stood up.

“Okay. I’m going to the arcade to meet up with some people. If you wanna hang out after work, I’ll be there.”

She put her hand on the back of Jess’ neck, slapping yet another loud, wet kiss on his open mouth, and then she was walking out of the gym, leaving Jess standing in front of the bleachers alone, like no one had ever been there in the first place.

He broke up with Shane later that night, after he had found Rory on the bridge and she told him what he had known for months now: she liked him. He liked her. And suddenly, it was just that simple.

He had wanted to pick her up off the ground and kiss her they way he’d been dreaming about for what felt like forever. He wanted to make up for every bit of time they had lost while they were with other people, while they were mad and fighting, while they weren’t _together_. But Jess, much as he liked to pretend otherwise, was a good guy. Okay, a sort of good guy. He was technically with Shane, which meant he couldn’t go around kissing other girls. He told Rory he had something to take care of, then headed to the arcade.

“Hey, we need to talk.”

Shane looked up from the Pac-Man screen, a confused look on her face. Their whole relationship had been based on not talking, so this was quite the about-face. Jess led her outside, nervous about how to do this. Technically, he had never broken up with anyone before; the girls had always broken up with him.

“I know this is shitty and, like, the biggest douche-move ever, but….” Jess let out a breath. “I can’t do this anymore.”

“Do what?” Shane had her arms crossed, a spark of realization in her eyes.

“This,” Jess gestured from himself to her. “It’s over.”

“You’re dumping me?” Shane shifted from one foot to the other, still seemingly calm.

“Uh….” Jess rubbed the back of his neck, feeling like a total scumbag. “Yeah. Yeah, I guess I am.”

“It’s Rory, huh?”

“What?”

“Come on, Jess,” Shane laughed. “I’m not an idiot. It’s obvious you like her. Now she and her boyfriend are split up, you’ve finally got your shot.” She shrugged. “It’s not like I didn’t know this was coming.”

“Shane, I-I didn’t mean to….hurt you, or anything,” Jess was surprised to find that he felt bad. He didn’t usually feel remorse for his actions, but something about this conversation felt like someone was twisting a knife in his heart.

“No, I’m okay,” Shane smiled. “We had fun, didn’t we?”

“Yeah,” Jess chuckled softly. “Yeah, we sure did.”

Shane took a step closer to him and kissed him softly. It was different from all the other kisses they had shared. This one wasn’t hungry and fast and begging for more. It was simple and sweet and Jess suddenly felt himself wondering about the girl Shane was, the person he had never bothered to get to know. She might have been a kindred spirit, a friend, someone to _actually_ talk to, but Jess had never taken the time to really see her.

“See you ‘round,” Shane stepped back, pulling open the arcade door.

“Yeah,” Jess was still trying to gather his thoughts and process the events of the past hour and a half. “Yeah, I’ll see you.”

Jess had dated Shane for 2 and a half months. He could barely remember her last name.

 

 

_v. Rory Gilmore_

Jess was seventeen years old and he had never felt this way about a girl before. Sure, they were kids and Rory’s path in life was markedly different than his own, but Jess saw the future when he looked in her eyes.

He left her. He still couldn’t tell you why he left, why he didn’t at least tell Rory where he was going, why he had to go. Maybe he didn’t want to disappoint her yet again. Maybe he knew that she would do anything to change his mind. But it doesn’t matter now, does it? He left the one person he had ever cared about like this, the one person who made him want to be the best version of himself. He didn’t have anyone to blame but himself and, trust me, he did.

Jess dated Rory for 7 months, 2 weeks, and 4 days. She was the first girl he had ever loved.

 

 

_vi. Eleanor Rigby_

Jess was eighteen years old and his heart was broken. He thought about Rory every day, but it wasn’t gonna do him any good. She was in Europe with her mom right now, and then she was going to Yale. She was going to go lead a great life. She was never coming back. So, Jess tried to distract himself. I mean, he dated her when he was a senior in high school! She couldn’t be “The One,” you know? He had too many years ahead of him; it wouldn’t be fair to love and lose his soulmate before he could legally drink.

He was at a music store, thumbing through the bargain rack of CDs and wishing it wasn’t so damn hot. Moving to California had seemed like a good idea at the time, but he was still getting used to the sun and the heat and the sand that got in his shoes and his pockets and in between the pages of his books. He missed New York. He missed Connecticut. He missed Rory.

Jess slammed the CDs in his hand back onto the rack, frustrated that he couldn’t seem to stop thinking about her for one goddamn second, and turned to go when a voice stopped him in his tracks.

“Didn’t find anything you liked?” He spun around to see a girl sitting behind the counter, one eyebrow raised.

“Nah, just….not in the mood.”

“Understandable,” the girl nodded. “I’ve seen you around.”

“Okay?”

“You’re always reading,” the girl blew a bright pink chewing-gum bubble.

“Gosh, you’re observant!” Jess widened his eyes in mock-admiration. “Does the FBI know you’re here? ‘Cause with eyes like that, they’ll be here any day now to recruit you.”

“Oh, piss off,” she rolled her eyes, moving out from behind the counter. “I mean, we get it: you’ve seen _Rebel Without A Cause_.”

Jess’ mouth fell open, struggling to come up with another zinger. Without Lorelai around to trade insults with, Jess had fallen a little out of practice. The girl wasn’t even paying attention to him anymore; she was scribbling something down on a Post-It note.

“Here,” she held the paper out towards him.

“What’s this?” Jess took the paper warily.

“You don’t like our selection, maybe you’ll like theirs,” she shrugged, straightening the CD rack that Jess had jumbled up. “Ask for Ronnie, tell him Eleanor sent you.”

“This is a little too Corleone family for me-”

“Shut up and get out of here,” the girl (Eleanor, he guessed) shoved him lightly. “Ronnie’s got good stuff; go scare off some of his customers.”

“Hey, I don’t scare off the other custo-”

“Give it a rest, Brando.” Eleanor pointed towards the door. “Come back with a better attitude and an original personality.”

Jess went to the record shop she recommended and she was right; they had good stuff. But he kept going back to Eleanor’s store. There was something about her that he liked, something that made his heart a little lighter.

After going to her store every day for two weeks, trying to work up the courage to ask her out, Eleanor finally came up to him.

“There’s a show at the Music Farm this Friday. The band’s supposed to be pretty good. Wanna come?”

“Uh-uh, yeah, sure,” Jess tried to sound smooth. “I mean, yeah, whatever.”

“Cool,” Eleanor looked like she was suppressing laughter. “Meet me in front of the store at 8.”

“Sounds good.”

“You were gonna ask me out, weren’t you?”

“Maybe.”

“You gotta work on your timing.”

“So I’ve been told.”

They went to the concert and Eleanor was right; the band was pretty good. And Eleanor was pretty; curly blonde hair, freckles, tons of silver jewelry. Eleanor was smart and sarcastic and Jess liked being in her company. So, when she kissed him at the end of the night, Jess liked that, too.

They dated all the summer, going to dingy, hole-in-the-wall venues for bands no one had ever heard of and then getting high on the beach afterwards. They had sex in her apartment, wrapping their arms around each other on a mattress on the floor while Bob Seger played in the background. With Eleanor, it was like being back in the 70s; smoking pot, having sex on the beach, and classic rock on a constant rotation. When Jess found out her full name was Eleanor Rigby, he had laughed in disbelief. It was like his own personal _Almost Famous_ . Eleanor was twenty, with three tattoos and a belly-button piercing. She basically ran the music store and she was saving up to buy it so she could _really_ be in charge.

Everything was good. Jess still thought about Rory, but sometimes he went a few days without her crossing his mind. He had told Eleanor about her one night. They were passing a joint back and forth, sitting on the beach and listening to the waves. Jess found himself launching into his whole sob story. Eleanor didn’t say anything until he finished.

“Well,” she brought the joint back between her lips. “That’s quite the Lifetime Original Movie there.”

“You got that right.”

“You’ll come back to each other,” she shrugged, tilting her head back to look up at the stars. “It’s fate, I can tell.”

Jess left it at that; as free-spirited and open as Eleanor was, it was just weird to discuss his ex with the girl he was currently dating. But Eleanor was strange like that, teasing out all the things he thought he had packed away in the dark corners of his soul. She never judged him; just listened with a thoughtful expression on her face.

Jess broke up with her in September. One day he had looked up and realized her eyes were the exact same shade of blue as Rory’s. That was all it took. He told her it was because he was leaving town, but something about those blue eyes unnerved him. It also unnerved him that it took him three months to realize she had blue eyes, but Jess chalked it up to all the weed. Either way, he decided to make his way back to Stars Hollow. He’d heard a rumor that Luke had his car and he’d need it to get all the way back to New York.

Eleanor took it well; just shrugged and said she figured California wasn’t exactly his scene. Jess knew they didn’t love each other; it was more like kindred spirits. They spoke the same way, carried themselves with the same “who gives a shit what you think?” swagger, and sorted their CD collections the same way (by genre). Eleanor had done his astrological chart or whatever the hell it was and told him they were so alike, it was scary. So maybe that’s why when he said he was leaving, she kissed him, slugged him lightly on the shoulder, and said, “Thanks for the good times, James Dean.” It was the same way Jess would have taken it, had Eleanor been the one to dump him.

Jess dated her for three months, give or take a few days. She was the first girl Jess had ever had sex with.  


 

_vii. Elizabeth Morland_

Jess was twenty years old and fresh off his latest rejection from one Rory Gilmore. You’d think he would have learned by now, but he just kept going back. Granted, he may have been a little overzealous; yelling at the girl you’ve loved for years now that you’re ready to love her right and that you should both just run away together is not necessarily a good way to show said girl that you’ve grown and matured. Whatever.

He was biking down 66th Street and cursing the day he had ever decided that being a bike messenger was an okay career option for the time being when he hit something. More like, some _one_.

“Holy shi-” Jess pretty much catapulted off his his bike, barely missing the trash cans that were to his right.

“Oh my God, I’m _so_ gonna kill you.”

Jess picked himself up off the pavement to see who was now threatening him with bodily harm and was amused to see a girl with glasses and a backpack almost as big as she was glaring up at him.

“Hey, sorry about that,” he stuck his hand out to help her up. “You just came outta nowhere.”

“Excuses, excuses,” the girl muttered, accepting Jess’ outstretched hand. However, instead of allowing herself to be pulled upright, this girl yanked Jess down onto the pavement with her.

“Jesus Christ!”

“Okay, I feel better now,” she smiled, slowly getting to her feet and brushing off her shirt. “Now, are you gonna help me pick up all the shit you knocked out of my hands?”

Jess, still trying to get his bearings with this weird girl, looked around and saw that he was, indeed, surrounded by notebooks, papers, and paperback books.

“What’s the backpack for?” He gestured towards it while gathering the loose materials with his free hand.

“Huh?” The girl looked up, blowing loose pieces of hair out of her face.

“Why have a backpack if you’re just gonna carry it all loose like this?”

“This,” she hefted a large stack of books onto her waist “is what doesn’t fit in my backpack.”

“So, you read a lot,” Jess picked up a copy of _The Collected Stories of Eudora Welty_.

“Yeah, I guess it comes with the territory,” the girl smiled for the first time. “I’m an education major, hoping to be an English teacher.”

Jess liked her smile. He liked the aura of disheveledness that surrounded her. So he wasn’t too surprised to hear himself saying, “Well, I feel like a real jackass for knocking you over like that. Want me to carry some of your books to wherever it is you’re going?”

As they walked the handful of blocks to her apartment, Jess found out a lot about this girl. Her name was Elizabeth Morland, she was a sophomore at NYU, she loved James Patterson novels and Thai food and, in no time at all, Jess had a crush.

He asked her out when they reached the doors of her building, some smooth line about a great Thai place that had opened in his neighborhood and would she wanna check it out?

Dating Elizabeth was the first real, grown-up relationship Jess had ever had. Going out with Elizabeth made him feel like an adult. He got haircuts more often and started dressing nicer. He got a checkbook. He quit his job as a bike messenger and got work as a temp in some corporate office building in Midtown. He went out with Elizabeth almost every day. They went to the Museum of National History a lot; Elizabeth would drag Jess along after her towards whatever weird exhibit she was obsessing over that week and, though Jess pretended to be annoyed, he liked it. They would order Chinese food to her apartment and he would read while she did her homework and it all felt so damn domestic, you’d think it would have sent Jess running. But he didn’t.

Sometimes, Jess would find flashes of Rory in Elizabeth; the stacks of books, the same beat-up sneakers, the way she tucked her hair behind her ears. But he managed to shake it all away. He liked Elizabeth _that_ much. He _loved_ Elizabeth.

They’d been dating for six months (he’d moved into her apartment a few weeks before. They had sex on the kitchen floor and Elizabeth laughed until she cried when Jess smacked his head on the counter)  when he told her, silently steeling himself for what he assumed was the inevitable rejection. But she just smiled and said, “I love you, too, Jess.”

And he thought that would be enough.

It had been about a year since they’d started dating and Jess knew something was wrong. Elizabeth wasn’t as happy and charmed by him anymore. She got mad when he left dishes in the sink for days at a time, or when she came home late from classes and work and he hadn’t taken care of dinner. They didn’t have sex on the kitchen floor anymore, either. Jess knew it was coming, but he looked away, trying not to see the next heartbreak that was coming up fast.

She broke up with him on a Wednesday night. They were sitting at the kitchen counter, silently eating cold pizza from a few days before, when she’d said, “Jess, we need to talk” and Jess could already see the end of it all.

He was numb and detached as Elizabeth went through her whole spiel, saying things like “You’re a great guy, but you won’t grow up” and “You keep hiding things from me and it makes me crazy” and “I love you, but I can’t do this anymore.”

He had thought that he had found something real here, something that would last. It was like life let him take one step forward and then knocked him two steps back. He should’ve known: life was never gonna be kind to Jess Mariano.

Jess moved out the next day. He had dated Elizabeth for just about a year. It was the longest relationship he had ever had. He had loved her so much, but he of all people knew that sometimes that just wasn’t enough.

 

 

_viii. Amy Quentin_

Jess was twenty-one years old and he didn’t know what he wanted anymore. He had written a book, if you can believe that. Well, more like a short novel. He was shopping it around to different publishing houses, but it wasn’t like he thought he had written the Great American Novel or anything.

He met Amy at a bar in Brooklyn. She was tall, with long red hair and thigh-high boots. Jess was instantly attracted to her and he went home with her that night.

They dated casually until one morning Amy got out a box of blueberry PopTarts and laughingly said that they were her favorite food. Too much like Rory. Jess dumped her the next day.

 

 

_ix. Jane Reynolds_

Jess met Jane at a Truncheon event. They dated for a month until Jess found out she had the same birthday as Rory.

 

 

_x. Nikki Quinn_

A one-night stand that ended as soon as Jess saw a copy of _The Fountainhead_ on her bedside table.

 

 

_xi. Leah Smith_

Spilled a drink on her shirt at a bar, dated for three months, broke up when Jess accidentally called her “Rory.”

 

 

_xii. Diana Owens_

Blind date set up by Matt, dated for two weeks, then Jess found out her mom’s name was Lorelai.

 

 

_xiii. Rory Gilmore (again)_

Jess was twenty-four years old and pretty sure that love was something that was meant for other people. Every girl he kissed in a bar or took home or spent any amount of time with would never last. He saw something of Rory in each of them and it was unsettling for him and unfair to them. He had given up the dating game. Oh sure, he had plenty of one-night stands. Girls liked dark, sad, troubled Jess Mariano. It was easy to get them into bed. He felt like a real tool afterwards but, hey; nothing’s perfect. This was his life and it was mostly pretty happy. Happier than he had ever expected, anyways.

He was walking home from Truncheon, enjoying the brisk night air and squinting to see the barely-visible stars, when he heard someone call his name. The voice was as familiar as his own, but he didn’t dare get his hopes up. There was no way. The last time he’d seen her was Truncheon’s first open house, when he’d kissed her and she told him she loved that blonde dick from Yale.

He turned around slowly and, as soon as he saw her, his heart started beating faster. It didn’t matter that they were older or that it had been a year and a half since they’d last talked; Jess felt like he was sixteen and seeing her for the first time all over again.

Rory walked up to him slowly, a sly smile on her face. “Wow, you really burn the midnight oil over at Truncheon, huh?”

“Matt and Chris are slave drivers,” Jess laughed nervously. “The Department of Labor is launching an investigation next week.” He paused, rocking back on his heels, waiting for Rory to say something. She didn’t. _Quite the role-reversal_. Jess cleared his throat. “So, not that I’m not happy to see you, but what brings you to my neck of the woods?”

“I’m in town on an assignment,” she said. “I’ve got a little down time and I thought I would see what you’re doing tonight.”

Even though they hadn’t talked in awhile, Jess still kept up on Rory’s life (through Luke, of course). He knew that she had dumped Blonde Dick From Yale after he publicly proposed to her, that she had gotten a job with a small website following Obama on the campaign trail, and now she was writing for them full-time. So it shouldn’t surprise him that she was here in Philadelphia, right?

He ended up taking her to an Italian place that was a few blocks away. The conversation felt a little stilted at first; Jess didn’t know what to do with his hands and Rory kept gulping her wine to fill the awkward silences. But soon enough, they settled back into the swing of their relationship and it felt good. It felt right. They talked about Lorelai and Luke, about their respective careers, and how strange it was to be here, together again. Jess didn’t add that this was a scenario that had played out in his dreams quite a few times. The night wore on and Jess was surprised to find that he was a little drunk. He and Rory had kept ordering more wine and now it was almost midnight and they were both slurring their words around the edges and laughing just a bit too loud. Jess liked it. He liked it a lot.

“God, we should have done this ages ago,” Rory smiled breathlessly, fiddling with the stem of her wine glass. “I forgot how much fun you are.”

“Wow, I’m honored,” Jess rolled his eyes.

“You know what I mean!”

“Yeah, I do.”

They left the restaurant after one of the waiters came over and said they were closing. Rory had laughed and announced “Another thing to check off the bucket list!” before making her way to the door, Jess following close behind her.

“I don’t wanna go back to my hotel,” Rory gathered her hair in a loose ponytail in her hands, then dropped it, letting it fall across her shoulders again. “Can we go back to your place for a drink?”

Jess’ mouth went dry. “Uh, y-yeah, sure.” he stuttered. “I think I can scare up some booze.”

Rory linked arms with him, said “There’s that Jess Mariano can-do attitude I know and love,” and then led him back up the street towards his building. Jess was too tipsy to fight it, but he knew he would regret this in the morning. Rory Gilmore was good for one thing in his book, and that was heartbreak. He was sure that he would wake up tomorrow morning with a splitting headache and a shattered heart, but that was sober-Jess’ problem. Drunk-Jess was gonna enjoy it while it lasted.

“Oh, of _course_ you’re a whiskey guy,” Rory laughed when she saw Jess filling their glasses.

“What’s that supposed to mean?”

“Nothing…..you’re just a walking cliche, that’s all.”

“I resent that.”

“I’m not surprised.”

Jess settled next to her on the couch, handing over her glass and taking a sip from his own.

“So, based on the groovy bachelor-pad decor you’ve got going on here, I’m guessing you’re not dating anyone?” Rory tucked her feet up under her and looked at Jess expectantly.

“Wow, we’re getting right to the uncomfortable stuff, huh?”

“Just curious.”

“Well, you’re right,” Jess pressed his lips together, hoping she would just leave it alone.

“Why not?”

“Rory-”

“I’m just asking,” she said, innocence dripping off ever word. Jess felt sick.

“Just haven’t found the right one yet,” he shrugged, knocking back another shot of whiskey.

“Why?” Rory was looking at him strangely; Jess couldn’t tell if that was pity or understanding in her eyes.

“Rory, I don’t think we should talk about this,” he sighed heavily, getting up from the couch and going to the kitchen. He didn’t know what for. He just knew he needed to be up and moving and not next to her.

“Why not?” Rory had stood up, watching him lean his hands on the counter.

“Because!” Jess was starting to get frustrated and angry and he needed her to leave _right now_ . He needed her to stay forever. Christ, he didn’t know _what_ he needed. “I can’t do this again, Rory, I can’t do this….this whole routine with you again!”

“What are you ta-”

“Who are you trying to get back at this time?” Jess narrowed his eyes at her, wishing he could stop himself. “I mean, Luke told me you and Logan are done, so who is it? Are you gonna kiss me again and then run back to him?” He squeezed his eyes shut. “I’m tired of being used, Rory. I can’t take it anymore.”

“Jess, I never meant to-”

“Yeah, I know you didn’t.” He smiled bitterly, half-enjoying the stricken look on her face. “You never do. And that’s fine. But I can’t do this again.”

“I wasn’t trying to get back at anyone!” Rory took a step closer to him, the kitchen counter still separating them. “I was just….I wanted to….”

“You wanted to what?” Jess was being short with her, but he didn’t care. If being a jerk was the only way he could protect himself, then that’s what he would do.

“There’s something wrong with me, Jess!” she finally burst out. Jess just stared at her. This was definitely not what he was expecting.

“Join the club.”

“No, you don’t understand,” she shook her head. “There really is something wrong with me, with my brain! I keep-I keep _hurting_ people and breaking _up_ with people and-and it’s because of you!”

“Hey, you don’t get to blame this on me!”

“No, no, that’s not what I mean!” Rory put a hand over her eyes, trying to gather herself. “I just mean….God, I don’t even know where to start.”

“Try the beginning.”

“If I’m gonna tell you, you gotta promise to stop interrupting me and to stop yelling,” Rory glared at him.

Jess raised his right hand. “Scout’s honor, ma’am.” He was interested to hear how Rory was going to lay the entirety of her life’s troubles at his feet.

Rory leaned her elbows on the counter. “So, you know I broke up with Logan.”

“I thought he dumped you.”

“It was mutual!” Rory snapped. “And you said you wouldn’t interrupt me!”

Jess mimed locking his mouth shut and throwing away the key.

“Anyways,” Rory sighed. “We broke up. And honestly, we’d been having problems before then. I think Logan thought he could just throw an engagement ring into the equation and I’d melt into his arms, you know? And I was considering it, I really was. I mean, Logan was fun and he thought I was the smartest person in the world and he loved me. I loved him, too.”

Jess rolled his eyes. “Not that I don’t find this _riveting_ , but can we SparkNotes it a little?”

“Hey, this is my story, I get to tell it how I want.”

“Whatever.”

“So, we broke up because I didn’t want to marry him.” Rory continued. “No one really faulted me for that because we were young and I had just graduated, for Pete’s sake! So, no one ever asked me _why_ I didn’t want to marry him.”

“Well, they all knew he was a grade-A prick, so I’m sure they weren’t too disappointed to see him go.”

“Old age really has not mellowed you.”

“Thank you,” Jess tipped his glass at her, a wry smile on his face. “So, why _did_ you reject his marriage proposal?”

“I didn’t know at the time. I just chalked it up to not wanting to be married and being unsure of Logan. But then I started dating again.”

“More millionaires, I hope.”

“Normal, working-class guys.”

“Bruce Springsteen would be so proud.”

“I started dating again,” Rory repeated, and Jess got the feeling she had been rehearsing this little monologue. She and Lorelai had always had a flair for the dramatic. “And I kept breaking up with guys. A few of them dumped me, but usually I would go out with them for a few months and then I’d call it quits.”

“It’s called modern dating.”

“No, that wasn’t it!” Rory widened her eyes. “I would break up with these guys for stupid reasons! For things that didn’t really even matter, except to me.”

Jess’ heart was thumping so loudly he was sure Rory could hear it. She was basically describing his romantic life since he’d left Stars Hollow. But she couldn’t be saying what he thought she was saying, right? That would be crazy.

“I broke up with one guy because he said Almost Famous was a dumb movie,” Rory laughed humorlessly. Jess’ mouth went dry. “I broke up with a guy ‘cause he told me he loved the small town he had grown up in. Hell, I broke up with a guy because he told me he hated Ernest Hemingway!”

“He sounds right up your alley.”

“Yeah, he had good taste.”

“So, what? You’re here to tell me that you break up with guys for random reasons because I broke some part of you when we were seventeen?”

“No!” Rory groaned. “Let me finish, okay?” Yeah, she had definitely rehearsed this. “I didn’t really know what it was; I just knew they weren’t right. And then I started thinking about Logan again and why I wouldn’t marry him and I realized….” Rory looked down. “I couldn’t marry him because _he_ wasn’t right.”

“Why wasn’t he right?” Jess was gripping onto the edge of the counter as hard as he could. He felt like he was gonna explode.

“Because….” Rory looked up at him, her eyes just as blue and shiny and wonderful as they were the first time Jess saw her. He felt like the ground was falling out from under him, like he was being pulled into a hurricane. He didn’t even care. “Because he wasn’t you.” Rory shrugged helplessly. “He wasn’t you.”

Jess just stared at her. He had to be dreaming, right? Or maybe he was just so drunk that he was hallucinating. Because there was no way that this could be real. Life wouldn’t be that kind.

“Jess?” Rory was still looking at him, apprehension on her face. “Jess, say something.”

With two quick steps, Jess was out from behind the counter and kissing Rory with all the strength he had in his body. He wrapped his arms around her, holding her so close that he was sure she could barely breathe. Rory’s hands were cupping his face and she was kissing him just as hungrily as he was. Jess didn’t care if this was a dream or a hallucination or a really realistic hologram. He just wanted this night to go on forever.

Even though he would have been happy to spend the rest of eternity making out with Rory, he slowly broke away, leaning his forehead against hers.

“Well,” Rory said with a shaky breath. “Good to know that still works, huh?”

“Do you mean it?” Jess didn’t have the patience to do their usual verbal parry-and-thrust. He needed to know the truth. “Are you really sure?”

“Jess, I’ve wrecked every chance at a real relationship I’ve ever had because, after all these years, you’re still in my head,” Rory still had her hand pressed against Jess’ cheek and the warmth radiating from it was the only reason Jess was pretty sure she wasn’t a hologram. “I wrestled with the thought of coming here for weeks because I was sure that you had moved on with your life, that you had forgotten me-”

“Never.” Jess smiled.

“I’m here.” Rory said simply. “I’m here and I’m tired of trying to love someone who isn’t you and I know what I want now.”

“And what is that?” Jess smile slyly.

“I want to be with you.” Rory smiled softly. “I’ve been running from you for too long and I don’t wanna waste anymore time.”

Jess kissed her again, more slowly this time. He wanted to savor every minute of this, to cement it all in his brain. He had taken so many turns, trying to get lost in life’s maze, but Rory had caught up with him in the end. She was here now.

“Rory?”

“Yeah?”

“Would you like to go out with me sometime? Maybe get dinner or something?”

“Jess,” Rory grinned, twining her arms around his neck. “There is nothing I would love more than to get dinner with you.”

This time, Rory kissed him and, to Jess, it felt like forever. The future that he had always seen so clearly in Rory’s eyes, Eleanor Rigby’s half-baked prediction that they would come back to each other; it was finally coming true.

Jess Mariano was twenty-four years old and he had been in love with the same girl ever since he was sixteen. They had fought and laughed and loved and lost and yelled and smiled and _been_ with each other for all those years. Maybe it was finally time for their happy ending.

Music swells. Fade to black. Roll credits.


End file.
